CA1196019A - Dihydric phenol recovery process - Google Patents
Dihydric phenol recovery processInfo
- Publication number
- CA1196019A CA1196019A CA000436793A CA436793A CA1196019A CA 1196019 A CA1196019 A CA 1196019A CA 000436793 A CA000436793 A CA 000436793A CA 436793 A CA436793 A CA 436793A CA 1196019 A CA1196019 A CA 1196019A
- Authority
- CA
- Canada
- Prior art keywords
- oxidizer
- organic phase
- dialkylbenzene
- caustic
- dihydroperoxide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000011084 recovery Methods 0.000 title abstract description 5
- 239000007800 oxidant agent Substances 0.000 claims abstract description 40
- 239000003518 caustics Substances 0.000 claims abstract description 34
- 239000012074 organic phase Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000008346 aqueous phase Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 7
- 230000003247 decreasing effect Effects 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 238000010926 purge Methods 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract description 14
- 239000012071 phase Substances 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 description 13
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 12
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 6
- REGMWDPZVFOJLY-UHFFFAOYSA-N 1,4-bis(2-hydroperoxypropan-2-yl)benzene Chemical compound OOC(C)(C)C1=CC=C(C(C)(C)OO)C=C1 REGMWDPZVFOJLY-UHFFFAOYSA-N 0.000 description 5
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- IROSBXFYXRIPRU-UHFFFAOYSA-N 1,3-bis(2-hydroperoxypropan-2-yl)benzene Chemical compound OOC(C)(C)C1=CC=CC(C(C)(C)OO)=C1 IROSBXFYXRIPRU-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241001290594 Caustis Species 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 210000004124 hock Anatomy 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- -1 resorclnol Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C407/00—Preparation of peroxy compounds
- C07C407/003—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C409/00—Peroxy compounds
- C07C409/02—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides
- C07C409/04—Peroxy compounds the —O—O— group being bound between a carbon atom, not further substituted by oxygen atoms, and hydrogen, i.e. hydroperoxides the carbon atom being acyclic
- C07C409/08—Compounds containing six-membered aromatic rings
- C07C409/12—Compounds containing six-membered aromatic rings with two alpha,alpha-dialkylmethyl hydroperoxy groups bound to carbon atoms of the same six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/427,972 US4670609A (en) | 1982-09-29 | 1982-09-29 | Dihydric phenol recovery process |
| US427,972 | 1982-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1196019A true CA1196019A (en) | 1985-10-29 |
Family
ID=23697062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000436793A Expired CA1196019A (en) | 1982-09-29 | 1983-09-15 | Dihydric phenol recovery process |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4670609A (enrdf_load_stackoverflow) |
| EP (1) | EP0105019B1 (enrdf_load_stackoverflow) |
| JP (1) | JPS5982327A (enrdf_load_stackoverflow) |
| CA (1) | CA1196019A (enrdf_load_stackoverflow) |
| DE (1) | DE3372855D1 (enrdf_load_stackoverflow) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI73194C (fi) * | 1985-11-19 | 1987-09-10 | Neste Oy | Foerfarande foer framstaellning av hydrokinon. |
| US4849549A (en) * | 1987-12-22 | 1989-07-18 | Indspec Chemical Corporation | Process for preparation of resorcinol |
| US4935551A (en) * | 1987-12-22 | 1990-06-19 | Indspec Chemical Corporation | Hydroperoxidation of diisopropylbenzene |
| EP0394813A3 (en) * | 1989-04-26 | 1992-04-08 | The Dow Chemical Company | Melt processable thermotropic aromatic copolyesters and process for preparing same |
| EP1440058B1 (en) * | 2001-09-19 | 2006-11-15 | Shell Internationale Researchmaatschappij B.V. | Process for preparing organic hydroperoxides |
| EP1636177A2 (en) * | 2003-02-28 | 2006-03-22 | Shell Internationale Research Maatschappij B.V. | Process for preparing organic hydroperoxides |
| WO2007094504A1 (ja) | 2006-02-16 | 2007-08-23 | Sumitomo Chemical Company, Limited | ジアルキルハイドロパーオキシベンゼンの製造方法 |
| JP4997787B2 (ja) | 2006-02-22 | 2012-08-08 | 住友化学株式会社 | フェノール類の製造方法 |
| CN112679403B (zh) * | 2019-10-18 | 2022-11-01 | 中国石油化工股份有限公司 | 制备间位二异丙苯二过氧化氢和对位二异丙苯二过氧化氢的方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB785607A (en) * | 1954-04-24 | 1957-10-30 | Distillers Co Yeast Ltd | Manufacture of organic hydroperoxides |
| GB893634A (en) * | 1959-07-13 | 1962-04-11 | Phenolchemie Gmbh | Improvements in or relating to the oxidation of aromatic compounds |
| BE608250A (enrdf_load_stackoverflow) * | 1960-09-17 | |||
| NL301578A (enrdf_load_stackoverflow) * | 1962-12-17 | |||
| US3376352A (en) * | 1963-02-21 | 1968-04-02 | Montedison Spa | Process for producing hydroquinone from p-dialkyl-benzene-bis-hydroperoxides |
| US3911020A (en) * | 1969-07-25 | 1975-10-07 | Goodyear Tire & Rubber | Process for the preparation of dialkylbenzene dihydroperoxide |
| US3968171A (en) * | 1970-03-05 | 1976-07-06 | The Goodyear Tire & Rubber Company | Process for the continuous isolation of dihydric phenols |
| US3883600A (en) * | 1970-05-04 | 1975-05-13 | Goodyear Tire & Rubber | Production of paradialkylbenzene dihydroperoxide |
| US4053520A (en) * | 1970-05-04 | 1977-10-11 | The Goodyear Tire & Rubber Company | Production of para-dialkylbenzene dihydroperoxide |
| US3882600A (en) * | 1971-04-01 | 1975-05-13 | Richard W Plymale | Composition in method for treating teeth |
| JPS59489B2 (ja) * | 1972-11-21 | 1984-01-07 | 住友化学工業株式会社 | ジハイドロパ−オキサイドの分解法 |
| US3978142A (en) * | 1974-01-14 | 1976-08-31 | The Goodyear Tire & Rubber Company | Process for producing polyphenols |
| JPS5136430A (en) * | 1974-09-20 | 1976-03-27 | Mitsui Petrochemical Ind | Hidorokinon no seiseihoho |
| DE2843957A1 (de) * | 1978-10-09 | 1980-04-17 | Huels Chemische Werke Ag | Verfahren zur herstellung von araliphatischen dihydroperoxiden |
-
1982
- 1982-09-29 US US06/427,972 patent/US4670609A/en not_active Expired - Lifetime
-
1983
- 1983-09-15 CA CA000436793A patent/CA1196019A/en not_active Expired
- 1983-09-19 EP EP83630157A patent/EP0105019B1/en not_active Expired
- 1983-09-19 DE DE8383630157T patent/DE3372855D1/de not_active Expired
- 1983-09-27 JP JP58179067A patent/JPS5982327A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0105019A3 (en) | 1985-10-30 |
| EP0105019A2 (en) | 1984-04-04 |
| DE3372855D1 (en) | 1987-09-10 |
| JPS5982327A (ja) | 1984-05-12 |
| JPH0253416B2 (enrdf_load_stackoverflow) | 1990-11-16 |
| EP0105019B1 (en) | 1987-08-05 |
| US4670609A (en) | 1987-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |